7 Big Men’s Style Mistakes We’ve All Made

July 10, 2012 By Joe| Heads up: Buying via our links may result in us getting a commission. Here's why.

1. Buying a suit that’s one size too large.

99% of us have made this $300 – $500 mistake. It’s usually our first adult suit, a sales associate in the Men’s section of a department store was helping us out, and we thought it looked pretty sharp at the time. Alterations would be done by their in-house tailors. It comes back, you wear it… and it fits you like a garbage bag. The shoulder pads are jutting out. There’s some contour at the waist, but you feel like you’ve got half a foot on either side. Sh*t.

2. Believing a shirt, tie, and dress pants = dressed up.

Yes it’s possible to look great wearing just a shirt and tie, but it’s not easy. A jacket of some sort is what most often separates the men from the boys stylistically. A shirt and tie is the homecoming dance uniform. That says a lot.

Just a shirt & tie can look unfinished. Suggestions for a little more, or a little less, here.

3. Getting a haircut a day or two before a big event

And of course, it doesn’t go as you had hoped. Wait until after the big day. Whatever it is. Of course you want to look your best on your wedding day, class reunion, big presentation at work, etc… but know that more often than not, us guys look our best a good week or two after we’ve gotten a trim. Plan accordingly.

4. Not knowing your measurements, and suffering the consequences

Similar to #1, but can result in bad shirt/pant purchases as well as awful fitting rental tuxedos. For example: I was lucky enough to stand up in a pal’s wedding more than a few years back. The wedding was out of town so I had to go get measured for a tux locally then pick it up from another shop after arriving on site. The employee measured me and called it in. The size she came up with? A 42. Long. I’m friggin’ 5’10” on a GOOD day. 165 pounds. Had no clue what it meant. I could have smuggled 5 kilos of blow across a border in that jacket. Knowledge is power. Know your sizes, and get some help from The Effortless Gent here.

5. Dry cleaning way too much

It’s absolute hell on fabric and construction, especially if you’re on a budget and wearing fused suits. Dry cleaning can melt that fusing, and when the fusing glue dries it’ll leave goofy looking wrinkles under the shell. It’s also really rough on wool. Unless your suit stinks of cigarettes, booze, or you’ve sweated like a pig in it, hang it up to air out then have it pressed or steam it yourself.

6. Wearing chunky, sporty sunglasses when dressed up.

It’s not quite like wearing running shoes with a suit, but it’s worth investing in a pair of wire frames or classic, slimmed down plastic frames like the New Wayfarer. You’ll look noticeably better at those summer weddings.

Well proportioned wire frames won’t lead you astray. Leave the sport shades at home when dressed up.

7. Putting too much stock in rules and lists

Like this very list perhaps? Anyway, getting dressed is a bit like cooking. There are three types:

Those who get intimidated by the whole damn thing, give up, and feel totally lost.

Those who strictly follow the ingredients and guidelines and get the job done.

Those who can improvise and put their own spin on a tried and true formula, or even wing it from scratch. Bravo to those who are okay if they have to scrap the final product. They enjoyed the attempt.

Lucky you if you haven’t made these mistakes along the way. Agreements, disagreements, and additions can go in the comments section below. Top Photo Credit:jepoirrier

Comments

Honestly? I think the shirt/tie/dress pants thing is bad mostly because the guys who do it are wearing bad pieces in all three slots. I don’t think it’s a very hard setup to look polished in! In fact, if a guy’s wearing nice, slim-fitting pants; a slim-fitting shirt; and a nice tie, *and* the colors and patterns are strong, I think it’d be kind of hard for him NOT to look good. The fit alone separates him from most others in identical outfits, so it’s not as though he needs to add extra pieces to distinguish himself further.

I have to agree with Jeff on the shirt and tie combo. If you wear ill fitting dress shirts, pants, and bad ties then yes, it can look bad. However if you get good piece I think it can look good.
I have made pretty much all these mistakes.

#1 Thanks to Dappered I’ve made a complete purge of all my old, ill-fitting suits (40R when I really am 38) and baggy dress shirts. Even my jeans and casual polos are now fitted and it’s amazing how much better I look and feel in them.

I agree. I find myself in a lot of situations where it would almost be inappropriate for me to wear a jacket, sometimes even a tie. I work in IT so a lot of people at work just wear polo shirts and chinos. If I walked in with a suit on I would look out of place unless I was a manager. The few occasions where it would be ok like an interview or a wedding or funeral or whatever, don’t come around too often. I have seen many guys wearing just nice shirts and pants and look very nice and not out of place and sometimes ties without jackets as well. I guess it just depends on the environment.

Yep, precisely. The shirt/tie/dress pants thing isn’t bad. Just when it’s the top level and the most dressed up a guy gets, and he wears it where there are plenty of guys who don’t top out at that, it can stand out. Speaking from personal experience on that one.

Still believe a well fitting jacket of some kind trumps a necktie sans jacket any day. Assuming they fit of course.

Justin, I have mixed feeling about your observation about the inappropriateness of you wearing a jacket. I first thought of those NBA players, who wear shorts and sneakers at “work” but most come and leave “suit up.”

I notice a few things that are congruent with the post. You feel good when you dress up. That leads to confidence, which shows in your body language, which gets notice by people around you, especially women. The post also mentioned that by dressing up you will more likely to be pulled by your manager for a client meeting. So wearing your jacket to lunch or while you are not down in the IT room, your benefit of being perceived higher than your peers (by your boss or non-IT employee), not to account the benefit of confidence, are too much not to attempt.

Another thing, typical guys will get over your wearing a tie/jacket pretty quick. They’ll bother you once, but that’s about it. They won’t even notice your oxford shoes. However, women and other sharp dressed men (usually higher position) will and those are the ones that will take you to the next level.

I won’t argue that you should care about appearance, I also feel it is important. Wearing a suit & tie however, is not automatically going to make him look good (as the post points out), nor will other wardrobe options automatically making him look “bad’.

To speak to Justin’s first example, and your reply, I work in QA currently and have worked in IT for many years. My company has a casual dress code, so many of our folks also come in wearing polos (or T-shirts). We have some folks who always look good, in shorts & polos, including our CEO.

When you say “They’ll bother you once, but that’s about it”, you’ve clearly never spent a significant amount of time in IT. There are always those people who will give you continual ribbing for ages over things they find silly. One IT guy in a suit amidst a sea of t-shirts and polos is very likely to get teased on a regular basis over this. In our company, you’re much more judged on the work you do rather than the shirt you have on. Overdressing makes us wonder what you’re trying to compensate for 😉

I agree…and this is one spot where 99% of all chinos are a bad choice to wear. Dress trousers make a huge difference when you just have a shirt and tie on….and, need we say, never wear short sleeve dress shirts…ever…

I agree that the shirt/tie/dress pants look can be done well. I wear it in the classroom as wearing a jacket while trying to teach is impractical for me (I move around constantly). I definitely think the distinction here is that I would not wear this getup to a wedding, or a fancy dinner party. Those are the instances in which well fitting jackets of some kind will always trump every other getup.

I agree with this 100%. While I do agree that wearing a suit will make me look nice and professional, this is not always the case in my field. I am always the best dressed at work in a nice button up dress shirt and dress pants and oxfords. A lot of people wear t-shirts and jeans. My last company had a casual dress code and people wore t-shirts, shorts, and flip flops to work. I would look silly coming to work in a suit when my boss has on a tshirt and shorts. You are judged by your knowledge and skills and not by what you dress in my field.

However, I do consulting and go from company to company and it just depends on the atmosphere. I don’t have anyone to impress with my clothes at work so there is no need for me to. I would love to wear a suit to work everyday and look sharp, but it does make you look like you are overcompensating for your lack of skills if you do this and you will get teased regularly by your peers. I might be able to get away with wearing a tie, but a tie and jacket just goes overboard where I am currently.

I used to believe this, but have come around to the view that others will always judge you in part by your dress — even if you don’t realize it, and even if *they* don’t realize it. That said, there’s a difference between dressing *well* and “dressing up.” The uniform is what it is, whether it’s suit and tie or shorts and polo. But given the uniform, it’s always possible to dress better (or worse) within it’s constraints.

I never suggested Justin to suit up. The only example was those in the NBA, who at one time I remember coming to work in jump suit. I merely suggested Justin not to be afraid of dressing one level up, which is what I took away from this article.

You’re right, I have never worked in IT environment, but even IT environment do corporate america, right? T-shirt, however, even in the most casual of IT, and I’m sure you may even agree, is pushing “casual” downward, don’t you think? So, if someone actually felt bad about comments from co-workers wearing T-shirts, we have bigger issues.

One level up can be many things. If you co-workers wear T-shirt, you wear polos. If your co-workers wear jeans, you wear khaki. If you co-workers wear khaki and shirt, you throw in a sport coat/jacket, and so on. In addition, this article mentioned something else that most men overlooked, the fit.

This is me, unfortunately, and will be until I can afford enough scratch to get custom-made shirts. My issue is that I’ve got a thick neck (18″) and long enough arms (35″) that the only off-the-rack shirts that will either have a neck too small, arms too short or the body of the shirt will be XXL (which is way too big for me). I know that I’m not pulling it off but my options are worse, at the moment

Number one is probably the worst epidemic facing style right now. Or more accurately its a symptom of that issue. The issue is men and fit. The insistence on larger baggier shirts, pants and jackets is distorting the shape of men’s clothes. Not only that but designers pick up on that sort of thing and new clothing lines are similarly distorted so that men can still but mediums and larges when the item is more true to large and extra large. Its getting difficult to find dress shirts that don’t require intense amounts of tailoring. I suspect all of this comes from body consciousness and self esteem issues. How this is to be conquered I don’t know. I’ve written about it on The Approach a lot. So have all the rest of the style bloggers but its not going away.

I just discovered this sight today and would like to weigh in on these mistakes. The shirt/tie/dress pants thing is fine if you are selling phones at Verizon, but a jacket is a must if you want to consider it dressed up. And I definitely still own my first suit that i bought because the octogenarian salesman said it looked great, only to reevaluate it later and saw it as a zoot suit. Mens Wearhouse is having a 50% suit sale right now when you donate an old suit to them. The donated suits are then tailored and given to men who need them for job interviews. I think this is a classy practice that more companies should implement.

Yes, I’ve never admitted it, but my mom took me to a discount suit place during grad school to get “interview suits”…I think I was hired despite those suits, and they sure served to educate me as to what wasn’t worth the savings!

I bought casual shoes during a buy one get one half off sale, and a suit-I-can-trash-if-needed, from a good rep named Kevin in Mission Viejo CA. I recommend him, though I recommend always choosing carefully in Men’s Warehouse

After wearing business casual the last 8 years, I realized the suits in my closet looked just like those on Friends: 3 button jackets going way up the chest, and wide lapels. No surprise: I bought them when Friends was in production!

There is absolutely a market for slender men’s shirts, but retailers just can’t afford to carry much inventory any more, especially in “odd” sizes. They can’t gauge the demand for all the times I’ve shown up and found nothing in my size. I’ve learned to show up when they get their shipments…what a waste of time having to befriend salesmen, shop on their schedule, and pay full price (since they sell out before the sales)! Hats off to dappered for alerting me to timely style on a budget!

You can look fine, just never particularly good. A good jacket is the whole point of wearing nice clothes. No garment flatters a man like a jacket. The jacket is far more important than everything else you put on.

Men’s Warehouse is fine. Would you look for something of extremely high quality there? No, if you do, then don’t whine. It’s affordable. Find one with an in house tailor, have it taken in, if you don’t like it, make them fix it.

I have great luck at my local MW. Besides the tailor you shouldn’t really need their associates, loathe is really hyperbolic thing to say.

A suit is one thing. I fully agree that a suit and tie when everyone else is wearing polos is overdressed and makes you stand out for all the wrong reasons. But a blazer is another thing. I’m a network engineer and I wear blazers all the time, sometimes with and sometimes without a tie.

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